The New York Times vs. OpenAI lawsuit is active and in discovery before the U.S. District Court for the Southern District of New York, with no trial date set as of mid-2026. Core copyright claims have survived dismissal, and the most consequential recent development is a court order requiring OpenAI to produce 20 million ChatGPT conversation logs to the Times and co-plaintiffs. Summary judgment briefing is expected during 2026, with a possible trial in 2027.
What the Times Is Actually Claiming
The Times filed suit on December 27, 2023, naming OpenAI and Microsoft as co-defendants. The complaint alleges OpenAI used millions of Times articles to train its GPT large language models without permission, and that the resulting products, including ChatGPT and Microsoft’s Copilot, can reproduce Times content nearly verbatim, closely summarize it, and mimic its style. The Times argues those tools function as substitutes for its journalism, letting readers bypass its paywall and undermining the business model that pays for its newsroom.
Microsoft is in the case because of its financial and operational entanglement with OpenAI. The Times alleges Microsoft invested at least $13 billion in OpenAI, serves as its sole cloud provider, helped build the supercomputing systems that trained the models, and deploys the technology across Bing, Microsoft 365 Copilot, and Azure AI.
The Times is seeking billions in statutory and actual damages, a permanent injunction, and destruction of any AI models and training datasets containing its content. On the licensing theory in the complaint, one analysis noted a $10-per-article rate applied to at least 16 million records would yield roughly $160 million in actual damages, while statutory damages for willful infringement can reach $150,000 per work.
Where the Case Stands
The case is The New York Times Company v. Microsoft Corporation, OpenAI, Inc., et al., No. 1:23-cv-11195, before U.S. District Judge Sidney H. Stein. Magistrate Judge Ona T. Wang is handling discovery.
The Times case has been consolidated for pretrial proceedings with two related suits: one filed by Daily News LP and other New York newspaper publishers on April 30, 2024, and one filed by The Center for Investigative Reporting in June 2024. A broader multidistrict litigation, In Re: OpenAI, Inc. Copyright Infringement Litigation, is proceeding in the same court and includes additional publishers such as Ziff Davis.
The docket was last updated in May 2026. The Times has begun reviewing the preserved ChatGPT logs it fought to obtain, OpenAI continues to contest discovery orders, and the fair use question at the heart of the case remains unresolved.
What Survived the Motions to Dismiss
OpenAI and Microsoft moved to dismiss several claims. Judge Stein ruled on the motions on March 26, 2025, and issued a detailed opinion on April 4, 2025.
The court let the core case proceed. It kept the direct copyright infringement claim alive, rejecting OpenAI’s argument that claims tied to 2019 and 2020 training were barred by the three-year statute of limitations; the court found OpenAI had not shown the plaintiffs knew or should have known about the alleged infringement by the relevant cutoff dates. The contributory infringement claim also survived, with the court finding the plaintiffs plausibly alleged OpenAI knew or should have known its users would infringe. State and federal trademark dilution claims brought by the Daily News plaintiffs were kept in the case as well.
Some claims were dismissed. Common law unfair competition claims were dismissed with prejudice across all three cases as preempted by Section 301 of the Copyright Act. Most Digital Millennium Copyright Act claims under Section 1202(b) were dismissed, though narrower claims about the removal of copyright management information survived in the Daily News and CIR actions.
A separate ruling on December 15, 2025, addressed Ziff Davis’s claims in the consolidated MDL. Judge Stein let Ziff Davis’s contributory infringement and several DMCA claims move forward, but dismissed its unjust enrichment claim and a claim that OpenAI circumvented technological measures by ignoring robots.txt files, ruling those files are “mere requests” rather than effective access controls. The court also stayed discovery on newer OpenAI models not yet part of the MDL, including GPT-4.5, GPT-5, and the o-series models.
The Fight Over ChatGPT User Logs
The most contentious phase of the litigation has been the battle over OpenAI’s user data. It has played out in two related tracks: a preservation order and a production order.
The Preservation Order
On May 13, 2025, Magistrate Judge Wang ordered OpenAI to “preserve and segregate all output log data that would otherwise be deleted on a going forward basis.” The order covered ChatGPT Free, Plus, Pro, and Team subscriptions, and API usage without zero-data-retention agreements. Enterprise and education customers were excluded.
OpenAI resisted. The company argued the order was disproportionate and technically burdensome, saying it would require preserving roughly 60 billion conversations when plaintiffs estimated only 0.006% might be relevant. OpenAI said compliance would take months of engineering work and cost millions of dollars, and would force it to override privacy commitments to users, including obligations under the GDPR. CEO Sam Altman said the decision “sets a bad precedent,” and COO Brad Lightcap said it “fundamentally conflicts with the privacy commitments we have made to our users.”
Judge Stein affirmed the preservation order on June 26, 2025. OpenAI complied by storing preserved conversations in a secured system accessible only to a small, audited legal and security team. The preservation obligation ended on September 26, 2025, after the parties negotiated a wind-down, and Judge Wang approved a stipulated modification on October 9, 2025. OpenAI kept a limited set of historical data from April through September 2025 but no longer has to preserve new conversations going forward. Data originating from the European Economic Area, Switzerland, and the United Kingdom was excluded from the retained set.
The 20-Million-Log Production
Separately, the Times and co-plaintiffs sought a large sample of ChatGPT conversations to test whether the tool routinely reproduces copyrighted content. In July 2025, they moved to compel 120 million logs. OpenAI counter-proposed 20 million logs scrubbed of personally identifiable information. Plaintiffs accepted the 20 million figure, but when OpenAI later refused to hand over the full sample and offered only keyword-based search results, the plaintiffs went back to court.
Judge Wang ordered production of the 20-million-log sample in November 2025 and denied OpenAI’s motion for reconsideration in December. On January 5, 2026, Judge Stein affirmed, ruling that Judge Wang’s decisions were “neither clearly erroneous nor contrary to law.” He found user privacy interests were adequately protected by three safeguards: limiting discovery to 20 million logs rather than tens of billions, OpenAI’s de-identification of the data, and the existing protective order. Judge Stein rejected OpenAI’s argument that the court must order the “least burdensome discovery possible,” and noted that ChatGPT users “voluntarily submitted their communications” and OpenAI’s possession of the logs was uncontested.
OpenAI’s Fair Use Defense
OpenAI’s central argument is that training AI models on copyrighted text is a “transformative, non-expressive analytical use” protected by fair use. The company says its models learn mathematical patterns, logic, and abstract relationships from training data rather than storing or reproducing source material. It characterizes instances where ChatGPT reproduces copyrighted text as a technical “bug” rather than a feature, and says it has added content filters and refusal training to reduce such outputs.
OpenAI points to two June 2025 rulings from California to support its position. In Bartz v. Anthropic, Judge William Alsup called AI training “transformative—spectacularly so” and granted summary judgment for Anthropic on fair use, though he found Anthropic’s acquisition of pirated books was not protected. In Kadrey v. Meta Platforms, Judge Vince Chhabria granted partial summary judgment for Meta on similar grounds but warned that a stronger evidentiary record on market harm could change the outcome in future cases. Both judges rejected the argument that lost licensing fees for AI training should count as market harm, calling the reasoning “circular.”
The Times case differs in ways that matter. The Bartz and Kadrey plaintiffs could not point to specific infringing outputs. The Times alleges that ChatGPT produces detailed summaries and near-verbatim excerpts of its reporting and functions as a paywall substitute. The Times also argues it lost licensing revenue in a market that demonstrably exists: the Associated Press, Axel Springer, the Financial Times, Le Monde, Prisa Media, and News Corp have all signed content deals with OpenAI, and OpenAI reportedly offered news organizations between $1 million and $5 million annually for training data licenses in 2024. The Times itself struck a separate multiyear licensing agreement with Amazon in May 2025, reportedly worth $20 to $25 million, for use of its content in Amazon’s AI products. Before filing suit, the Times spent nine months negotiating with OpenAI; OpenAI has said a “high-value partnership” was close.
Not every recent decision has gone the AI companies’ way. In Thomson Reuters v. Ross Intelligence, decided in February 2025, a Delaware federal court rejected fair use where the defendant used copyrighted legal headnotes to build a direct competitor to Westlaw, finding the use substitutive rather than transformative. That case is on appeal to the Third Circuit.
Settlement Prospects and What to Watch
No settlement has been publicly reported between the Times and OpenAI. Legal commentators generally view a negotiated resolution as more likely than a full trial, given the financial exposure for OpenAI and the cost and risk of extended litigation for both sides. Michael Bennett of the University of Illinois Chicago has predicted the Times will ultimately settle, partly because of the benchmark effect of Anthropic’s $1.5 billion class settlement in Bartz. That settlement covers roughly 500,000 pirated books at about $3,000 per work, requires Anthropic to destroy the pirated files, and does not grant a license for future training; as of mid-2026 it awaits final approval, with Judge Alsup having expressed concern over insufficient detail in the allocation plan. Settlement estimates for the Times case from legal analysts have ranged from $2 billion to $5 billion, though those figures are speculative.
The next major milestones to watch are summary judgment briefing during 2026, the Times’s analysis of the 20-million-log sample now in its hands, and any ruling that squarely addresses fair use in the context of news journalism, a question no court has yet answered.